Trifluoroacetic acid → HCID 86708651, compound

HRID 1430947Notes

Reaction equation

HRID 1430947 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C:16]1[C:17]([Cl:38])=[C:18]([CH:33]=[C:34]([C:36]#[N:37])[CH:35]=1)[CH2:19][N:20]1[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]1)=O)(C)(C)C>C(Cl)Cl>[NH2:15][C:16]1[CH:35]=[C:34]([CH:33]=[C:18]([CH2:19][N:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]2)[C:17]=1[Cl:38])[C:36]#[N:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708652HCID 86708652, compound

Product 1

HCID 86708651HCID 86708651, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.0 mL) was added to a solution of tert-butyl 4-(3-((tert-butoxycarbonyl)amino)-2-chloro-5-cyanobenzyl)piperazine-1-carboxylate (59 mg, 0.13 mmol) in DCM (1.0 mL) at RT. After 1 hr, the solvent was removed and the residue was dissolved in MeOH and applied onto an SCX column. This was washed with MeOH and the product was eluted with 2N NH3 in MeOH to give 3-amino-4-chloro-5-(piperazin-1-ylmethyl)benzonitrile (22 mg) as an oil.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue was dissolved in MeOH
  3. washThis was washed with MeOH
  4. washthe product was eluted with 2N NH3 in MeOH

Sources & evidence

ORD record
ord-a42720f48c004b958f751955e3837214
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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